


Pretty Pictures

by TheMockingCrows



Category: Homestuck
Genre: Crossdressing, Feeding, Light Bondage, M/M, Masturbation, Oral Sex, thigh highs
Language: English
Status: Completed
Published: 2013-06-11
Updated: 2013-06-11
Packaged: 2017-12-14 16:05:02
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,562
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/838758
Author URL: https://archiveofourown.org/users/TheMockingCrows/pseuds/TheMockingCrows
Summary: <blockquote class="userstuff">
              <p>Last time they fooled around, John got to choose where and when and how. When Dave proposes a less than standard photoshoot with his boyfriend for his turn, it's hard to say how John will react. After all, it's only a dress.. right?</p>
            </blockquote>





	Pretty Pictures

At first, the promise had been an easy one. Dave had said it would be a simple trade for indulging John's interest in public sex, still bearing the marks on his pale neck from buck teeth nipping at him as they fooled around a hairs breadth from being discovered in the clubs bathroom. Thank god the other patrons had been more than a little drunk, thinking nothing of the four feet and the rattling door as a sign of strong drinks and great music banging through the walls.

People who were stupid drunk were likely to become a common saving grace of theirs in the next few years. Maybe the rest of their lives, depending on how their habits strayed on remained the same.

The simplicity of the promise had grown harder and harder to weigh as an even trade as extras were added on. Panties and some thigh highs had been the original deal, with the promise of photos Dave could take of him while he wore them. A pair of heels were requested to go with them, for the sake of the photos appeal apparently. No height was ever specific, nor style. When the request had gone even higher, however..

“NO.”

“Come on, why not?”

“Because no.”

“Dude, I'm not asking yes or no, I'm asking why. Color me curious.”

John glared into the webcam, lips turning out in a pout. Dave had his shades up on his head, and his hair was sticking up in funny directions since he hadn't brushed it. According to their talk earlier, he'd woken up at almost noon and immediately crawled to his computer to start running photoshop on some pictures he'd taken, wanting to clean parts of them up and run some filtering to make the edges sharper before removing most of their color.

He was pretty damn sure that if he gave Dave enough time he'd wind up with a handful of inspired work, a fuck ton of hipster photos, and thousands of bastardized custom Blingee gifs. The hushed scraping and sliding sound of his pen on the tablet as he worked the image over how he wanted were comforting to listen to, but they weren't the answer John wasn't going to give.

“C'mon, babe, what's wrong with the dress idea. You'd even get to pick which dress you wanted, which heels. Fuck, man, toss a bow on for all I care. Call it a surprise,” he said far too casually. Dave was distracted, talking about getting his boyfriend to cross dress and pose for him as if he were discussing the weather or an interesting new television show that would start up in the next season. Coupons for an extra burger on his receipt from McDonalds. Finding a five dollar bill in his pocket.

Where was the extra coercion? The lewd comments, the usual jokes? This was so un-Dave-like that it was concerning. No rambling mile a minute with loose string connections. Just.. a comment as he worked here and there, almost bored. It got under John's skin.

“Oh, right. Of course. Okay. I'll find a dress and shoes because I obviously know what sizes I am and where the heck to buy these kinds of things. That's completely something I'm used to doing, Dave, definitely in my range of knowledge,” John said, voice dripping with sarcasm.

Without missing a beat, perfectly serious, Dave said, “Rad, I'll be sure to get the film by next week and we can pick a date. I'm thinkin' blanket fort tea party or some shit.”

It took patience for John not to grind his teeth and work his jaw harder in frustration, finally dropping the tone to be blunt. Dave seemed to respond better to that tone whether he was busy or not.

“Alright then, Dave. That was a fib. I don't know anything about dresses, or shoes, or any of that crap. I don't have any sisters or anything, and Rose doesn't talk about anything like that with me. Jade's as much a guy as either of us anymore, dresses can't keep up with her without getting in her way. I'm.. not really sure what I'm needing.” He hurried added, “I'm also not sure if I'm saying yes yet!”

“What colors would you be cool with?” Dave asked. “Blues, whites, black, greys?”

“I don't really look good in black shirts, it makes me look pale,” he said. The only dark clothes he really looked good in were suits and jeans with a light shirt.

“Skirts. Not shirts. Dresses. Dark skirt would probably look good on those skinny ass legs of yours,” Dave said. More soft scratching, tapping from his pen. Editing, maybe selecting, or even adding dots and texture to a background. “Though, white'd bring out your eyes more, make the highlights in your hair stand out. Maybe pastel instead.”

“....Dave, look, I appreciate the sudden knowledge of color coordination with my features, but. Uh. That doesn't really solve the whole size problem. Not to mention that I'm still not sure if I'll even do i-”

“You're about the same size as I am, just a bit broader in the shoulder. It should fit. Worst case scenario is it's a bit tight on the shoulders, and we'd have to switch to a blouse with a skirt instead. You got your own stockings, or do you need those too?”

John frowned and leaned back in his seat, letting the chair squeak.

“Dave, are you filling an Amazon shopping cart or something for this?”

“Why would I buy new when I've got extras?”

“Extra what?”

“Hey, John. Date night. Let's make it Friday night, okay? I'll show up with bells on, and we'll make a night of it. Maybe call for a pizza, I'll bring some cash to split the bill after. Gotta go ahead and finish this up real quick, love ya, bye. 

The words came out in a rush before the skype call abruptly ended, and John's attempts at calling him back were met with the same amount of success as the sudden wave of text that was left unanswered. No ring had popped up beside the text. It had gone through and was received properly instead of remaining in the sending stage, signaling that Dave was hidden instead of really offline.

Sneaky son of a bitch.

John found himself daydreaming over the next few days, trying to sort out the meaning of Dave's almost cryptic words. Extras? Extra.. clothes? Shoes? Maybe he meant from Rose. After all, they'd been close for years and they were even closer since she and Kanaya had started dating. She might be the go to person for clothing ideas or hand-me-down's. Hopefully Dave would do the asking instead of making him do it. He wasn't so certain he could handle going up to his friend and bluntly asking, “Hey, Rose, I know I used to have a crush on you a few years back but can I have your clothes so I can cross dress with my boyfriend and he can take illicit pictures?”

Friday afternoon, Dave texted him at last.

 

TG: morning

EB: i think you mean afternoon, dave. it's past noon already!

TG: if i just woke up it counts as morning

TG: im gonna bend the english language and its jacked up meanings to suit my needs

EB: well then! good morning to you too, destroyer of an already jacked up language! your deeds will forever be remembered as pointless.

TG: youre so sweet to me it stings

EB: i know, i'm the best boyfriend ever.

TG: so tonights the night right

EB: …. well..

TG: can you order stuffed crust for the pizza

TG: ive got a mean hankering for stuffed crust holy shit

TG: ill bring some soda and stuff too so dont worry about that

TG: everything on their menu for desserts is hella greasy and i dont want these things getting stained up forever

TG: you think you can manage kitten heels???

TG: i dont trust your ass in anything more without training wheels and like

TG: inch deep carpet or more

TG: they should fit unless youre a wide

TG: i cant remember if youre a wide or not all i can remember about your feet is theyre hella cute

TG: might be able to stand a bit of polish at some point maybe some electric sex blue to match your eyes

EB: dave.

TG: have you ever actually read the labels on some of those things???

TG: holy shit its like reading a harlequin novel or a cookbook half the time

TG: or a lineup of ke$has new albums if you hit the glitter section

EB: dave.

TG: though once you hit the high brands they go from cutesy names to business and then back to cutesy

TG: theres no middle ground for spiced pumpkin or candy apple red

TG: i wonder if any high society chicks or little old ladies foray into the realm of electric sex blue and hot tamale red???

EB: DAVE.

TG: what

EB: stuffed crust pizza. ordered. will be here about seven. will you be?

TG: with bells on

\- - - - -

Bells on was thankfully not literal. Dave turned up in loose sweatpants and a hoodie pulled low over his face, a shopping bag full of Little Debbie cakes and soda, and a small suitcase on wheels. John helped him thump everything upstairs and got a plate for the cakes so they could unwrap them, lounging in the living room afterward as they waited for the pizza to arrive. Dave never opened the suitcase, and he never brought up the clothes or plans for the evening. He never took off his hoodie, or his shoes, which were normally the first things to go when he came over. Something about enjoying a clean floor without having to worry about booby traps or bits of foam and fleece getting between his toes.

Only after the pizza had arrived and been paid for did they go back upstairs, Dave chattering away, John interjecting things and responding when he got the chance in the tidal wave. They unwrapped the cakes from the boxes and arranged them on the plate, strawberry shortcakes and tasty morsels drenched in stiff white icing. Like a sculptor, Dave arranged them how he wished, checking them from different angles.

“Dave. They're cake. They're cheap cake that taste like sugar and fake fruit, why all the care?”

“They're props, Eggs. Let the photographer work.”

Artists. Bah.

John happily stuffed his face as Dave worked, straddling his computer chair to avoid dribbling on his bed or leaving too many crumbs. Dave asked for a piece and they ate in silence for a while as he moved and tweaked the snacks by millimeters, checking the lighting. He debated the position of the lamps, the window with its dying light of summer, and finally stood up to dust his hands off, and quickly drop his pants.

John almost choked, looking over at Dave as it dawned on him that his legs were covered with something skin tight and striped like candycanes up to his pale thighs. His groin was covered in what looked to be a soft set of similarly striped red panties, and as the hoodie was drawn up and over his head, his torso was circled by a well fitted red corset. It slimmed him down, made the sharp jut of his hips appear smoother by comparison, and proved to be a beautiful distraction for John. Toeing off his shoes and removing the pants entirely at last, Dave went and crouched by the suitcase, unzipping it.

“John? Get naked.”

“I... What?”

“Picture time. Get naked.”

“But-!”

“Or do you wanna wear two sets of clothes? Can't put a dress on you if you're already wearing stuff. Naked please.” He gestured with his hand for a moment, a rotating gesture implying 'come along, please'.

Hesitant, John stood and dusted his hands off on his jeans to get rid of residue from his pizza, then started to ditch his clothes to the corner. When he was left in his boxers, he awkwardly crossed his arms over his front to watch Dave work out clothes from the case without making them wrinkled. There was a good amount of different shades of blue, though the majority seemed to be a pale color of the sky, along with white and some black items as well. A neatly folded set of striped panties to match, and a set of long white socks came out as well.

Dave helped him put everything on properly, working the panties up and into place when John squawked at him indignantly, getting the knee highs rolled up when he got them tangled up on himself from inexperience. The slip and petticoat were simple to get on, but left John in giggles for some reason, the barely laced ends tickling him terribly. By the time they were done, John was perched stunned on the edge of his bed with a bow in his hair, looking like a re-imagining of Alice out of her Wonderland, dazed and shivering. Trying to stay calm and clear his head.

It helped that Dave got dressed as well, asking only that John dig his iPod out of his pocket and put some music on for them. Maybe lock the door if he would be so kind. Dave wound up in a re-imagining of card suits, the dress white on the base and lined with black on the edges. The divided sections of the skirt held large pictures of the card suits, with the sash at his waist being pictures of the classic Queen, King and Jack. He settled a Joker pin in his hair with a crown barrette on the other side.

John... had to admit, he looked good. They both did, actually. The dresses weren't poorly made, nor were they terribly puffy or covered in lace and bows. Simple. Subdued. Natural, but elegantly... pretty. When Dave pulled out a small black bag from inside the suitcase, he assumed it would be some jewelery or something. He never expected it to be makeup, and protested in annoyance when Dave came at him with it.

“I draw the line at mascara, Dave! You said dress! DRESS. This is more than a dress!”

“Total effect, babe, don't worry. I'm good at this.”

“...Dave, how are you good at this, and where did you get these?”

“Rose uses me as a dress up dummy for her clothes designs when she's doing fittings, and it turns out? I like it.” He coerced John by reminding him that this was private, and what they'd done at the club could have landed them both in handcuffs with wilted dicks, and finally got him painted up with natural makeup and a pale pink lip stain. For himself, he was careful to remove his shades and replace them with a smoky tinted rectangular set.

He took out his camera and a tripod, and made a fuss setting up basic lighting with the lamps in John's room, guiding it where he wanted it to go for the shots. They'd be taking them on John's bed for the most part, and he was just as obsessive with trying to make it look as casually messy as possible by painstaking arrangements once he made John stand up.  
  
The heels proved to be a little tight on him, but thankfully, he wouldn't have to try walking in them whatsoever. Just sitting, posed, for the pictures. Dave had him sit and strike a pose looking off from the camera, lost, and snapped a few test shots to get the proper feeling before he set to work. Holding his knees, one shoe half off with his legs crossed, holding a cake and looking at it with a sleepy smile. Ten shots in and everything was perfect.. till the handcuffs came out.

John eyed them warily, not remembering that being on the list.

“Uh.. Dave. What're those for?”

“Next part of the photoshoot, just relax. If you get too tense or somethin', just tell me and I'll pop them right off for you,” Dave said with a grin, setting the timer and a series of auto-shoots on his camera as he went and sat by John. The first picture went off after he'd taken his seat and reached for him. Another when he put the first cuff on. Another when he crawled seductively behind him and cuffed the second. Another when he perched next to the cake plate and lifted one. A final when he took a bite from one of the white icing clad confections as if it were the tastiest treat in the world. Licking his lips, Dave hopped off the mattress and turned off the mechanism, then crossed and unhooked one of John's wrists.

He grinned and looked up expectantly.

“Was that all?” Wow. That was easier than he thought. Now they'd just sit around and.. eat pizza in dresses, he guessed. That was the way things were apparently going.

That's not the way things were going at all. Dave leaned over him heavily and kissed his mouth, breathing out through his nose as he balanced one hand on the bed and ran another up and down John's side, fingers skipping along like he was playing an instrument. John responded like the unheard music, groaning up into his mouth, arching and twisting his body up into the familiar touch. Unfamiliar circumstances, but hey. What was wrong with a little make believe? A little dress up?

Make believe was the last thing on John's mind when Dave slid one of his legs between John's thighs and pressed him back into the bed with a sigh, moving from his mouth to the column of his throat to kiss down the length of it. He kissed gently at his hidden collarbones, not wanting to smudge his own lipstick on the fabric, and kneaded at his hips and thighs. When John started to rock his hips, he huskily murmured for him to sit upright so he could help him out of the dress.

Off came the apron and the dress, the petticoat and the slip. The bow stayed put. Dave went behind him once more, reaching around to his front to rub at his stomach and chest, licking a stripe up the back of his neck.. before clicking the cuffs back into place and pulling away without warning. Clad in lingire and knee socks, John sat stunned in handcuffs with his erection, staring at his boyfriend as he moved to the camera to set the timer again. It took him longer, setting a higher number, longer space between shots.

“DAVE! Come on, take this off, this isn't cool!”

“Why? Dude, nobody will ever see these but us.”

“.....You promise?”

“Yeah, of course. You're gorgeous, man. The only shots anyone will see, you're fully clothed. Photoshoot is done.. this is extra curricular.”

Ignoring the occasional flicker and click of the camera, Dave tormented John. Mouthing his erection through the panties till he was shuddering and rocking his hips at the air, shoulders rolling to try getting loose so he could touch himself. He pulled his dick out so it rested above the edge of his panties, and licked a stripe from his thigh to his throat, nibbling, ignoring where he wanted to be touched the most.

He struggled when Dave fed him cakes, putting up a valiant effort before timidly giving in and accepting the sweet treats. The knowledge he could say no at any time was comforting, Dave always quick to tease and sweet talk, stroking him gently while he chewed the cloyingly sweet cakes.

“A..ahh.. Dave.. Fuck. Dave!”

Another click of the camera as Dave settled between his legs once more, his own ankles crossed behind him and his dress gone, stroking himself in time with the deliberate suckling he was giving to John as he writhed and rolled in his handcuffs. The suckling was battling with John's attempts to fuck his throat out of instinct, trying to get into the warmth and tightness that was being offered to him so readily. The next click and flash of the camera went off when he cried out and thrust his hips up towards Dave's face, making him gag and back off to swallow hurriedly. After another minute of working himself over, Dave finished as well against the bedsheets and his own hand, crawling up John's body to lay atop him and kiss at his lips hungrily.

The last picture was the one that Dave broke his promise and showed the world, mostly because it didn't show their faces. It showed two slender bodies clad only in lingire, afterglow, sweat and sleep. Stockings and socks were falling down, panties pushed aside, Dave's corset still comfortably in place. Their hair was mussed, legs and arms intertwined, the plate of cakes undisturbed. It was beautiful in a way, a lively party of dolls collapsed in one each other once the magic left.

Beautiful.

But not beautiful enough to save John from chewing Dave out for the surprise cake and handcuffs trick, swearing up and down that he'd think up something really good for the next time he got to choose. Dave just grinned.

“Oh, good. Here's hoping you keep me on my toes.”

**Author's Note:**

> original tumblr post- http://themockingcrows.tumblr.com/post/52704005349/pretty-pictures  
> Fan art!- http://cactuspr0n.tumblr.com/post/52733797598/yup-finished-enjoy-im-hiding-from-tumblr-the


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